After joining the Jedi Order, Cloak became a Padawan under the teachings of Master Xak. Cloak and Xak formed a strong bond and learned alot from eachother. When his padawanship was almost complete, Master Xak along with others were expelled from the Order for voicing out their disagreement with the council. Cloak took this hard, but at the request of his Master, he remained in the order to complete his training under Master Wind. While remaining 'a good padawan' Cloak continued his training in under Master Xak in seceret.
Cloak was Knighted not long after his Master and friends expultion from the Order. He remained in the order for some time before taking on his first padawan, Teela. Cloak felt the force had brought Teela and him together, and appeared he was right, as with his own Master, the two formed a bond rivaling any master and padawan before their time. During the time of Teelas padawanship, The Battle of Naboo broke out in which the two of them, along with other Jedi they recruitd to the cause, played a key role in culminating in the liberation of the world.
During this time, Cloak began to suspect corruption in the Enclave Council, and like his master, was expelled along with Teela from the Order for their accusations, though not before Teela was Knighted and Cloak himself made a Master. It was then that The two started theGrey Jedi Order. Unlike the grey Jedi of the past, the Orders members were not inbetween light and dark, but rather Jedi of the light that did not agree with the Council. As the corruption in the Jedi Order grew, and rumors that Cloak and his paawan had truned to the darkside, Cloak left Tatooine for a time, and traveled to the High Council hidden on Tavias. Cloak presented his case and concerns to the High Council. The Corruption was quickly put to an end by the Council, after which they asked Cloak to take on the head position of the Council Enclave on Tatooine.
Cloak accepted this request, and returned to Tatooine and started the Jedi Watchmen branch of the Order there. After a long period of hardships, the Watchmen grew into a small yet strong and loyal group of Jedi Knights and continues to grow.